Water → HCID 19992265, compound

HRID 345485Notes

Reaction equation

HRID 345485 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1.Cl[CH2:24][CH2:25][C:26]([N:28]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27].C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O.[I-].[K+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)([OH:9])[CH:10]2[CH2:11][CH2:12][N:13]([CH2:24][CH2:25][C:26]([N:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:27])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 33314083-chloro-N,N-diphenylpropanamideHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanol

Product 1

HCID 19992265HCID 19992265, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 12.0 g (0.040 mole) of α,α-bis(4-fluorophenyl)-4-piperidine methanol, 10.3 g (0.040 mole) of 3-chloro-N,N-diphenylpropanamide, 17.0 g (0.160 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 100 ml of N,N-dimethylformamide was heated on a steam bath for 16 h. The mixture was poured into 2 L of water and a solid precipitated. After standing 3 h, the solid was collected by filtration, washed with water, dried and recrystallized from benzene-petroleum ether (30°-60° C.) to yield 18.7 g (90%) of a white solid, mp 160°-162° C.

Workup

  1. temperaturewas heated on a steam bath for 16 h
  2. customa solid precipitated
  3. filtrationthe solid was collected by filtration
  4. washwashed with water
  5. customdried
  6. customrecrystallized from benzene-petroleum ether (30°-60° C.)

Sources & evidence

ORD record
ord-3cbf1f674b0d42fbb9f55e113c8f7f08
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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